Traveling from Hampton to Winchester covers 205.8 miles and typically takes about 4 hours and 19 minutes behind the wheel. Given the duration, this trip is perfectly manageable as a single-day excursion, though you might prefer an overnight stay if you want to explore Winchester at a relaxed pace. You will start your journey in the Southeast region of Virginia before heading toward the northern part of the state. Budgeting approximately $33 for fuel will cover your transit costs for the trip. Since the route requires navigating local roads like West Pembroke Avenue and North Armistead Avenue before connecting to I-64 West, expect a mix of city driving and highway travel. It is a straightforward trek that connects the coastal area to the Shenandoah Valley region, making it an efficient way to cross the state.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
102.9 miles from Hampton, VA
A natural place for your longest stop of the day
, about 1h 56m into the drive
.
Main Roads
Road
Distance
Duration
I 64
61.1 mi
1h 7m
I 95
47.3 mi
51m
Warrenton Road
22.9 mi
33m
US 17
12.9 mi
19m
Korean War Veterans Memorial Highway
11.9 mi
12m
James Madison Highway
11.3 mi
15m
John Singleton Mosby Highway
8.9 mi
12m
Millwood Pike
5.7 mi
9m
Longest stretch:
I 64
— 61.1 mi, about 1h 7m
Turn-by-Turn Driving Directions
Step-by-step road directions between Hampton, VA and Winchester, VA.
1
Start on North King Street
126 ft·5 sec·North King Street
2
Turn left onto VA 351
0.3 mi·42 sec·West Pembroke Avenue
3
Turn right onto VA 134
0.9 mi·1 min·North Armistead Avenue
4
Take the ramp
0.3 mi·44 sec
Toward I 64 WestUse the left lane.
5
Merge onto I 64
2.5 mi·3 min·Hampton Roads Beltway
Use the straight / slight right lanes.
6
Keep slight left at fork onto I 64
61 mi·1 hr 7 min·I 64
Use the straight / slight right lanes.
7
Take the exit
0.5 mi·32 sec
Exit 200Toward I 295, US 60: Washington, Rocky Mount NCUse the straight / slight right lanes.
8
Keep slight right at fork
1.3 mi·2 min
Toward I 295 North: WashingtonUse the straight / slight right lanes.
9
Merge onto I 295
12 mi·12 min·Korean War Veterans Memorial Highway
10
Take the exit
2.4 mi·2 min
Exit 43AToward I 95 North: WashingtonUse the slight left lane.
11
Merge onto I 95
46 mi·49 min·I 95
Use the straight / slight right lanes.
12
Keep slight right at fork onto I 95; US 17
1.6 mi·1 min·I 95; US 17
13
Keep slight right at fork
0.3 mi·41 sec
Toward US 17 Business: Falmouth
14
Turn left onto US 17
23 mi·33 min·Warrenton Road
Use the straight lane.
15
Continue on US 17
4.2 mi·7 min·Marsh Road
16
Turn right onto US 15; US 29
4.6 mi·6 min·James Madison Highway
17
Continue on US 15; US 17; US 29
2.4 mi·3 min·Eastern Bypass
18
Keep slight right at fork onto US 17
2.3 mi·3 min·Eastern Bypass
Toward US 17 North
19
Continue on US 17
6.7 mi·9 min·James Madison Highway
20
Continue on US 17
2.7 mi·3 min·Winchester Road
21
Turn left onto US 17
4.8 mi·5 min·US 17
Use the left lane.
22
Take the exit onto US 17; VA 55
8.1 mi·13 min·US 17; VA 55
Exit 23Toward US 17 North: Delaplane, ParisUse the straight / slight right lanes.
23
At end of road, turn left onto US 17; US 50
8.9 mi·12 min·John Singleton Mosby Highway
24
Continue on US 17; US 50
2.1 mi·3 min·John Mosby Highway
25
Continue on US 17; US 50
5.7 mi·9 min·Millwood Pike
Use the left / straight lanes.
26
Continue on US 17; US 50; US 522
0.2 mi·20 sec·Millwood Avenue
27
Continue on US 17; US 50; US 522
0.8 mi·1 min·Millwood Avenue
28
Turn right onto South Kent Street
0.6 mi·1 min·South Kent Street
29
Turn left onto East Boscawen Street
427 ft·18 sec·East Boscawen Street
30
Turn right onto US 11; US 522
0.1 mi·25 sec·North Cameron Street
31
Arrive at destination
US 11; US 522
Trip Plan
To make the most of your 4-hour and 19-minute transit, plan your departure to avoid peak local traffic, especially when navigating the initial turns on West Pembroke Avenue. Since the route includes one planned stop, use that time to stretch and refuel your vehicle, keeping your $33 budget in mind for mid-trip fill-ups. Because the drive is a single-day commitment, you have the flexibility to adjust your start time based on your personal preference for morning or afternoon travel. Keep a close watch on your GPS during the first leg, as the local road transitions are the most complex part of the navigation. Taking this approach ensures you reach Winchester feeling fresh rather than fatigued from the technical nature of the early segments.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 102.9 miles from Hampton, VA, or about 1h 56m into the drive.
The longest continuous stretch on this route runs about 61.1 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 45 miles or 52m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 102.9 miles or 1h 56m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 3h 23m
Traffic, exits, and arrival timing usually matter more near Winchester, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Hampton, VA so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Hampton, VA
This is one driving day of about 205.8 miles and 4h 19m.
Your first comfortable stop window is around 45 miles from Hampton, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on I 64 for about 61.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 20
5 decision points cluster between mile 3.9 and 179.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
3.9 mi into trip|~6m in|I 64
Keep slight left at fork onto I 64
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
8
65 mi into trip|~1h 14m in
Take the exit toward I 295, US 60: Washington, Rocky Mount NC
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 200
Toward I 295, US 60: Washington, Rocky Mount NC
7
65.5 mi into trip|~1h 14m in
Keep slight right at fork toward I 295 North: Washington
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward I 295 North: Washington
7
78.7 mi into trip|~1h 30m in
Take the exit toward I 95 North: Washington
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight left lane.
Exit 43A
Toward I 95 North: Washington
8
179.3 mi into trip|~3h 36m in|US 17; VA 55
Take the exit onto US 17; VA 55 toward US 17 North: Delaplane, Paris
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 23
Toward US 17 North: Delaplane, Paris
Fuel & Cost
Regular Gas
$32.18 one way
$64.37 round trip
$3.97/gal25.4 MPG avg72 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$35.19
$70.38
premium
$4.70
$38.09
$76.18
diesel
$5.61
$45.44
$90.88
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$32
Meals
$25–$50
Total
$57–$82
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 72 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $22 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
61.7
0
$21.61
$9.88
Efficient EV
51.5
0
$18.01
$8.23
EV Truck/SUV
82.3
1
$28.81
$13.17
Gas CO2
72 kg
EV CO2
24 kg (67% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 14, 2026
Origin
Hampton, VA
Late night
in Hampton on Sunday
Local time
1:57 AM
EDT
Current temp
64°F
Partly Cloudy
SW 12 mph2% chanceLive forecast
Destination
Winchester, VA
Late night
in Winchester on Sunday
Local time
1:57 AM
EDT
Current temp
83°F
Unavailable
Live forecast
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
19 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
4h 19m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Colonial National Historical Park
National Historical Park
On May 13, 1607, Jamestown was established as the first permanent English settlement in North America. Three cultures came together – European, Virginia Indian and African–to create a new society that...
0 mi from route
~1 min detour
$15
near mile 21.3
Park Closure: Rehabilitation of Colonial Parkway Continues
Fort Monroe's story spans from prehistory to the 2000s. Kecoughtan Indians occupied Old Point Comfort before the arrival of English colonists. The first enslaved Africans arrived in 1619. Those escapi...
Cedar Creek & Belle Grove National Historical Park
National Historical Park
Virginia’s Shenandoah Valley has a long and rich heritage that still inspires today. Native Americans first shaped the land, followed by colonists and settlers. The fertile valley became an important...
12 mi from route
~30 min detour
Free
near mile 198.7
At the confluence of the Shenandoah and Potomac rivers, on the ancestral home of the Tuscarora and Shawnee people, lies Harpers Ferry. Here you can explore John Brown's Raid against slavery. Find your...
24 mi from route
~59 min detour
$20
near mile 191.7
Two hundred ninety-two days, eight offensives, over 70,000 casualties, U. S. Colored Troops, and the decline of Gen. Lee's Army of Northern Virginia all describe the Siege of Petersburg. U.S. forces c...
26 mi from route
~65 min detour
Free
near mile 63.9
The Potomac River corridor is rich in both history and recreation, offering a chance to both explore your heritage and choose your adventure along the way. Start your journey here!
26 mi from route
~65 min detour
Free
near mile 184.6
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a turn-heavy local drive that demands your full attention as you navigate out of the Hampton area. Unlike a monotonous interstate slog, this route requires you to transition from local streets like North Armistead Avenue onto the larger I-64 West corridor. While the highway percentage is currently listed at zero, the logistics of the drive rely heavily on these initial local connections before settling into your main transit path. You will notice the character of the road shifts significantly as you leave the urbanized Southeast corridor behind. Be prepared for a driving experience that feels more technical than a standard cross-country interstate cruise, requiring you to remain alert through various turns and transitions throughout the 205.8-mile journey.
59% highway, the rest on surface roads — varied driving throughout.
31 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 61.1 mi on I 64.
How Hard Is This Drive?
9/10
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 3.9 miles in near I 64.
Driving Effort9/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 20 significant decision points across 205.8 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 3.9 miles (I 64): Highway fork - watch signs carefully. Lane positioning matters here; at 65 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 65.5 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Hampton, VA and Winchester, VA, road signs point toward Rocky Mount and Paris.
Rocky Mount
65 mi in|~1h 14m
Paris
179.3 mi in|~3h 36m|via US 17; VA 55
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 4h 19m. Total distance: 205.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 19m drive, comfortable solo distance.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 61.1 miles on I 64. The full list of main roads is in the Roads section above.
Yes — we found about 1 rest area or service plaza within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Winchester, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. There are 1 rest area along the route for bathroom stops.
The main spots that need attention: at 3.9 miles (I 64): Highway fork - watch signs carefully. Lane positioning matters here; at 65 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 65.5 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Colonial National Historical Park, Fort Monroe National Monument and Cedar Creek & Belle Grove National Historical Park (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.3 hours each way, an in-and-out day trip would put you behind the wheel for 8.7 hours — manageable with a long break at Winchester, VA, but most travelers stay overnight.
